GB1117110A - Improvements relating to acid anthraquinone dyestuffs and their use - Google Patents

Improvements relating to acid anthraquinone dyestuffs and their use

Info

Publication number
GB1117110A
GB1117110A GB54330/65A GB5433065A GB1117110A GB 1117110 A GB1117110 A GB 1117110A GB 54330/65 A GB54330/65 A GB 54330/65A GB 5433065 A GB5433065 A GB 5433065A GB 1117110 A GB1117110 A GB 1117110A
Authority
GB
United Kingdom
Prior art keywords
alkyl
formula
mol
group
compound
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB54330/65A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Novartis AG
Original Assignee
JR Geigy AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by JR Geigy AG filed Critical JR Geigy AG
Publication of GB1117110A publication Critical patent/GB1117110A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
    • C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
    • C09B62/465—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being an acryloyl group, a quaternised or non-quaternised aminoalkyl carbonyl group or a (—N)n—CO—A—O—X or (—N)n—CO—A—Hal group, wherein A is an alkylene or alkylidene group, X is hydrogen or an acyl radical of an organic or inorganic acid, Hal is a halogen atom, and n is 0 or 1
    • C09B62/467—Anthracene dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/16—Amino-anthraquinones
    • C09B1/20—Preparation from starting materials already containing the anthracene nucleus
    • C09B1/207—Dyes with amino groups and with onium groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/16—Amino-anthraquinones
    • C09B1/20—Preparation from starting materials already containing the anthracene nucleus
    • C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
    • C09B1/28—Dyes with amino groups substituted by hydrocarbon radicals substituted by alkyl, aralkyl or cyclo alkyl groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/16—Amino-anthraquinones
    • C09B1/20—Preparation from starting materials already containing the anthracene nucleus
    • C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
    • C09B1/28—Dyes with amino groups substituted by hydrocarbon radicals substituted by alkyl, aralkyl or cyclo alkyl groups
    • C09B1/30—Dyes with amino groups substituted by hydrocarbon radicals substituted by alkyl, aralkyl or cyclo alkyl groups sulfonated
    • C09B1/306—Dyes with amino groups substituted by hydrocarbon radicals substituted by alkyl, aralkyl or cyclo alkyl groups sulfonated only sulfonated in a substituent
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
    • C09B5/02—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic ring being only condensed in peri position
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
    • C09B5/02—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic ring being only condensed in peri position
    • C09B5/14—Benz-azabenzanthrones (anthrapyridones)
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
    • C09B5/24—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position
    • C09B5/42—Pyridino anthraquinones
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/92—Synthetic fiber dyeing
    • Y10S8/924—Polyamide fiber

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises acid anthraquinone dyestuffs of the formula <FORM:1117110/C4-C5/1> wherein R1 is a secondary alkyl or cycloalkyl group, R12 is an aralkyl group which may be ring-substituted by C1-C4 alkyl or alkoxy, or halogen and it can be monovalent when R13 is aralkyl, otherwise it is polyvalent; R13 is an alkyl, cycloalkyl or a monovalent or polyvalent aralkyl group optionally ring-substituted by C1-C4 alkyl or alkoxy, or halogens; R4 is H or C1-C4 alkyl, A is an alkenyl group optionally containing at least one substituent which can be split as an ion, which alkenyl radical can be further substituted or it represents an alkyl group containing at least one substituent which can be split off as an ion, which alkyl group may be further substituted, m and n each represents 1 or 2, and in so far as R12 and R13 contain a sulphonic acid group and a group <FORM:1117110/C4-C5/2> they are linked to these groups by a ring carbon atom. They may be obtained by (1) condensing an anthraquinone compound of the formula <FORM:1117110/C4-C5/3> wherein X is a Cl, Br, OH, C1-C4 alkoxy, NO2 or amino group, with an aralkylamine containing at least two exchangeable hydrogen atoms in the aryl moiety, of the formula <FORM:1117110/C4-C5/4> wherein R2 is an aralkyl group optionally ring-substituted by C1-C4 alkyl or alkoxy, or halogens and R3 is an alkyl group, a cycloalkyl group or an aralkyl group optionally ring substituted by C1-C4 alkyl or alkoxy or halogens, to form the corresponding 1-sec. alkylamino- or 1 - cycloalkylamino - 4 - aralkylaminoanthraquinone compound and, in any order, condensing this with n mol. of sulphonating agent and with m mol. of a compound of the formula <FORM:1117110/C4-C5/5> (2) condensing an anthraquinone compound of the formula <FORM:1117110/C4-C5/6> wherein Y is an acyl radical, with an aralkylamine of Formula II to form the corresponding 1 - (N - sec. alkyl - N - acylamino)- or 1 - (N-cycloalkyl - N - acylamino) - 4 - aralkylamino-anthraquinone compound and, in any order, saponifying and condensing this with n mol. of a sulphonating agent and m mol. of a compound of Formula III or a reactive functional derivative thereof; (3) condensing an anthraquinone compound of the formula <FORM:1117110/C4-C5/7> wherein W is a Cl, Br, OH, C1- 4 alkoxy, NO2 or amino group with a sec. alkylamine or a cycloalkylamine of the formula <FORM:1117110/C4-C5/8> to form the corresponding 1-sec. alkylamino- or 1 cycloakylamino - 4 - aralkylamino - anthraquinone compound and, in any order, condensing this with n mol. of a sulphonating agent and m mol. of a compound of Formula III or a functional derivative thereof; and (4) condensing an anthraquinone compound of the formula <FORM:1117110/C4-C5/9> with a sec. alkylamine or a cycloalkylamine of Formula VII to form the corresponding 1-sec. alkylamino- or 1 - cycloalkylamino - 4 - (N - aralkyl - N - acylamino) - anthraquinone compound and, in any order, saponifying and reacting this with n mol. of a sulphonifying and reacting this with n mol. of a sulphonating agent and m mol. of a compound of Formula III or a functional derivative thereof. Specified acyl groups for Y are carbacyl groups, e.g. alkanoyl or aroyl radicals, alkyl- or aryl-sulphonyl radicals. Specified substituents which may be split off as an ion, i.e. cation or anion, are halogens, alcoholic hudroxyl esterified with sulphuric acid or with aliphatic or aromatic sulphonic acid, or the groups R-O-, R-S-and R-SO2, wherein R is an organic radical; quaternary ammonium groups, the group <FORM:1117110/C4-C5/100> Examples are given for the production of the dyes. They may be used for dyeing or printing natural or synthetic polymide fibres blue shades, and also for the dyeing of cellulos materials.
GB54330/65A 1964-12-22 1965-12-22 Improvements relating to acid anthraquinone dyestuffs and their use Expired GB1117110A (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
CH1653364A CH446568A (en) 1964-12-22 1964-12-22 Process for the preparation of acidic anthraquinone dyes
CH1663364A CH466470A (en) 1964-12-22 1964-12-23 Process for the preparation of acidic anthraquinone dyes
CH856866A CH485813A (en) 1964-12-22 1966-06-14 Process for the production of new dyes
CH1576668A CH471853A (en) 1964-12-22 1966-06-17 Process for the preparation of acidic anthraquinone dyes
CH884166A CH473183A (en) 1964-12-22 1966-06-17 Process for the preparation of acidic anthraquinone dyes

Publications (1)

Publication Number Publication Date
GB1117110A true GB1117110A (en) 1968-06-12

Family

ID=27509340

Family Applications (4)

Application Number Title Priority Date Filing Date
GB54330/65A Expired GB1117110A (en) 1964-12-22 1965-12-22 Improvements relating to acid anthraquinone dyestuffs and their use
GB54058/65A Expired GB1102789A (en) 1964-12-22 1965-12-31 Improvements relating to acid anthraquinone dyestuffs and their use
GB27536/67A Expired GB1188378A (en) 1964-12-22 1967-06-14 Dibenzonaphthacridine-5,11,16-Trione Derivatives and processes for their manufacture and use
GB27914/67A Expired GB1160812A (en) 1964-12-22 1967-06-16 Improvements relating to Acid Anthraquinone Dyestuffs and their use

Family Applications After (3)

Application Number Title Priority Date Filing Date
GB54058/65A Expired GB1102789A (en) 1964-12-22 1965-12-31 Improvements relating to acid anthraquinone dyestuffs and their use
GB27536/67A Expired GB1188378A (en) 1964-12-22 1967-06-14 Dibenzonaphthacridine-5,11,16-Trione Derivatives and processes for their manufacture and use
GB27914/67A Expired GB1160812A (en) 1964-12-22 1967-06-16 Improvements relating to Acid Anthraquinone Dyestuffs and their use

Country Status (8)

Country Link
US (4) US3431285A (en)
BE (3) BE674121A (en)
CH (5) CH446568A (en)
DE (2) DE1644542A1 (en)
ES (1) ES341913A1 (en)
FR (4) FR1461168A (en)
GB (4) GB1117110A (en)
NL (5) NL6516628A (en)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3872137A (en) * 1969-03-18 1975-03-18 Fidelity Union Trust Company E Anthraquinone compounds
US3671529A (en) * 1969-08-20 1972-06-20 Sandoz Ltd Basic anthraquinone dyes, with pyridinium 2- or 4-dimethylene group
BE794893A (en) * 1972-02-04 1973-08-02 Ciba Geigy ANTHRAQUINONIC COMPOUNDS REACTING ON FIBER, THEIR PREPARATION PROCESS AND THEIR USE
DE2307591C3 (en) * 1973-02-16 1982-05-13 Bayer Ag, 5090 Leverkusen Anthraquinone compounds, their preparation and their use
DE2513950A1 (en) * 1975-03-29 1976-10-14 Bayer Ag METHOD FOR PRODUCING ANTHRACHINONE COMPOUNDS
DE2730342C3 (en) * 1976-07-07 1980-12-18 Ciba-Geigy Ag, Basel (Schweiz) Process for the preparation of anthraquinone compounds
CH634088A5 (en) * 1978-04-07 1983-01-14 Sandoz Ag ANTHRACHINONE COMPOUNDS AND THEIR PRODUCTION.
US4693727A (en) * 1984-11-08 1987-09-15 Ciba-Geigy Corporation Process for dyeing synthetic polyamide materials with fibre-reactive anthraquinone dyes
EP0181293B1 (en) * 1984-11-08 1990-10-24 Ciba-Geigy Ag Process for dyeing synthetic polyamide materials with anthrachinone reactive dyes
US4652269A (en) * 1984-11-08 1987-03-24 Ciba-Geigy Corporation Process for the continuous trichromatic dyeing of synthetic polyamide materials: including a blue anthraquinone reactive dye
US5248808A (en) * 1989-11-01 1993-09-28 Avery Dennison Corporation Vinyl functional reactive tackifiers for pressure-sensitive adhesives
EP0601970A1 (en) * 1992-12-03 1994-06-15 Ciba-Geigy Ag Anthraquinone dyes, process for their manufacture and use thereof

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2426547A (en) * 1943-04-12 1947-08-26 Ici Ltd Anthraquinone dyestuffs
US2475530A (en) * 1946-03-18 1949-07-05 Ici Ltd Process for making aminoanthraquinone sulfonic acids
US3030369A (en) * 1953-06-08 1962-04-17 American Cyanamid Co New vat dyes
NL121826C (en) * 1959-07-24
NL270721A (en) * 1960-10-28

Also Published As

Publication number Publication date
BE674121A (en) 1966-06-21
GB1160812A (en) 1969-08-06
NL6708435A (en) 1967-12-18
BE674182A (en) 1966-06-22
DE1644542A1 (en) 1971-02-11
GB1102789A (en) 1968-02-07
DE1644543A1 (en) 1971-02-25
US3530135A (en) 1970-09-22
US3499915A (en) 1970-03-10
NL130308C (en)
ES341913A1 (en) 1968-12-01
CH446568A (en) 1967-11-15
CH485813A (en) 1970-02-15
NL131932C (en)
FR1527542A (en) 1968-05-31
DE1644522A1 (en) 1969-10-23
DE1644552A1 (en) 1971-02-25
CH471853A (en) 1969-04-30
US3431285A (en) 1969-03-04
NL6516861A (en) 1966-06-24
NL6516628A (en) 1966-06-23
US3538128A (en) 1970-11-03
FR1525542A (en) 1968-05-17
BE700052A (en) 1967-12-18
FR1461168A (en) 1966-12-02
FR1461853A (en) 1966-12-09
GB1188378A (en) 1970-04-15
CH473183A (en) 1969-05-31
CH466470A (en) 1968-12-15

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